摘要
阴离子在化学、医药、环境和生命活动中发挥着非常重要的作用,设计和合成对阴离子具有选择性识别和传感作用的人工受体是当前迅速发展的研究领域之一。大量含有不同识别位点的非生物的阴离子识别主体被设计、合成出来。其中一类非常重要的识别主体是含咪唑盐单元的化合物。咪唑盐可以通过(C-H)+…X-这种离子化的氢键与阴离子发生作用。同等情况下,它与阴离子的作用强度要大于文献报道较多的中性识别位点吡咯、酰胺、脲／硫脲等与阴离子之间的作用。阴离子识别的发展不仅取决于对不同类型主体的构建,还有赖于围绕某种特定离子进行合理化设计的努力。近年来,对生物和环境具有重大影响的阴离子如CN-的识别,传感,检测越来越受到人们的关注。因此,本文追踪当前阴离子识别的热点,分别从基于咪唑盐的不同类型主体的构建和CN-识别方面展开研究。
本文分为四部分,第一部分详细地阐述了阴离子识别的发展、识别的主要作用力、研究方法、在化学传感器方面的应用等,分别介绍了以咪唑盐作为主体和以氰根作为客体的研究现状。在评述阴离子识别理论和研究进展的基础上,提出了论文工作设计。
在第二部分,我们以咪唑单元为识别位点,分别以二茂铁,萘/喹喔啉/蒽,对硝基苯基为电化学,荧光和比色信号单元,构建了10种阴离子传感器。其中,既有双臂主体(4-7),也有环状主体(8-13)；既有单纯的电化学传感器(4,6,8-10),也有电化学-比色(5),电化学-荧光(7,11-13)这样的多信号传感器。5,7,11-13为我们首先合成的基于咪唑盐的多信号传感器,解决了以往传感器信号单一,可识别离子单一的问题。
所有主体化合物结构均通过单晶衍射的证明。在晶体中,主体可通过咪唑2,4,5位的CH,亚甲基上的CH和二茂铁上的CH来识别阴离子。核磁滴定表明,在液相中,主体主要通过咪唑2位的CH来与客体形成氢键。主体8较为特殊,与客体的作用有赖于苯环2位氢与咪唑2位氢的协同作用。苯环2位氢化学位移之变化达到1.2 ppm。电化学研究表明,主体4,8-13可通过氧化电位的减小选择性地识别F-,△Ep>214 mV,还可通过还原电流的显著增强来识别HS04-。主体8可通过荧光增强的现象来识别F-和AcO-；通过紫外光谱的红移现象来识别H2P04,△λ=8 nm。
第三部分工作中,我们以客体为中心,围绕CN-识别与传感展开工作。首先,我们以缺电子的三氟乙酰胺基为氰根识别单元,以两种常见的比色基团即对硝基偶氮苯基和蒽醌为信号单元,构建了对硝基偶氮苯类主体23和蒽醌类主体26,27。核磁滴定表明,主体与CN-作用机理为CN-对缺电子的羰基碳的亲核加成,形成的氰醇氧负离子与胺基NH形成氢键从而稳定产物。蒽醌类主体26中由于NH与蒽醌羰基氧形成较强的分子内氢键,从而形成较稳定的六元环。胺基NH无法与亲核进攻形成的氧负离子很好的作用,使反应无法很好的向正反应方向进行。因此,主体26是一个很好的反例,设计时应避免此种情况的出现。我们研究了CN-和其它11种常见无机阴离子存在下主体的紫外及比色性质。主体23和27可在水环境中高选择性的识别及传感CN-。这种选择性是由CN-两方面的性质决定的,即强的亲核性和弱的溶剂化能。此外,主体23和27对CN-的检出限也比较低,达到微摩尔级别。因此,这两个主体是检测水环境中低浓度CN-的理想的比色传感器。
最后一部分,我们将商品化的花菁染料作为氰根识别库。核磁滴定表明,CN-可与花菁染料亚胺部分发生亲核加成反应。主体的大共轭结构遭到破坏,从而引起光学性质的极大改变。我们可以通过主体溶液变色现象和荧光淬灭现象来“感知”CN-的存在。
三次甲基花菁染料28和五次甲基花菁染料29可在非质子性有机溶剂中和二氯甲烷／水两相体系中高选择性和灵敏度地识别CN-。但它们在含水均一体系中表现不佳。七次甲基除在以上两种体系中能有效识别CN-外,还可以在乙腈／水缓冲溶液中和含有Triton X-100的纯水缓冲溶液中识别CN-。次甲基链变长有助于提高主客体反应活性这一现象为我们进一步设计基于花菁染料的传感器提供了非常重要的指向。
应该指出,我们这一体系在识别CN-方面有很多优点1)主体为商品化试剂；2)集比色传感与荧光传感与一身；3)选择性高,常见干扰物F-,AcO-等无干扰；4)非常灵敏,可通过两相策略检测水中微摩尔级别的CN-,主体30还可通过表面活性剂辅助法来检测出纯水中低于1.9μM的CN-,检出限方面相对于已有报道有很强优势；5)近红外区传感,主体29和30可在近红外区传感CN,这方面报道还很少。
Anion recognition is currently an expanding area due primarily to its important roles in modern chemistry and life processes, as well as in many medical and environmental settings. Accordingly, development of synthetic receptors with high binding affinity and selectivity or good sensing properties for anionic species is an important goal for researchers. Various kinds of receptors with different binding units have been designed and synthesized. The imidazolium group is an attractive building block for anion receptors because it contributes one relatively strong hydrogen bonding site. Unlike those most commonly utilized anion binding groups such as neutral (thio)urea, pyrrole, amide which form N-H...X-hydrogen bonds, imidazolium group can interact with anions through (C-H)+...X- type ionic hydrogen bonds. Recently, numerous efforts have been devoted to the study of imidazolium derivatives as anion receptors. The development of anion recognition chemistry depends not only on the construction of different kinds of receptors, but also on the efforts of rational design center on specific guest. Recently considerable attention has been paid for the recognition and sensing of guests that have important influence on life and environment.
The dissertation is divided into four parts. In chapter one, the development and application of anion recognition and imidazolium-based receptors as well as the progress of cyanide recognition have been reviewed in detail.
In the second part,10 anion chemosensors were designed and synthesized by utilizing imidazolium groups as anion binding sites, ferrocene group as electrochemical unit, naphthalene, quinoxaline or anthracene as fluorescent groups and p-nitrobenzyl group as colorimetric subunit. Compounds 4-7 are cleft-like receptors, while compounds 8-13 belong to cyclic receptors. There are three kinds of sensors, i.e. electrochemical sensors (4,6,8-10), electrochemical/colorimetric sensors, and electrochemical/fluorescent sensors (7,11-13).5,7,11-13 are first reported imidazolium-based multisignaling sensors.
All receptors were characterized by X-ray crystallography. In the solid state, these receptors can interact with guests through hydrogen bonds formed between C2H, C4H, C5H, methylene CH or ferrocene CH and anions.1 H NMR titration
revealed that, in the solution state, receptors interacted with anions mainly through (C-H)+...X- type ionic hydrogen bonds. In the case of 8,benzene C2H can cooperative with imidazolium C2H toward anions. Significantly downfield shifts (A8 =1.2 ppm for AcO) were observed for the C-2 proton of the benzene ring. Electrochemical studies demonstrated that all the receptors showed effective electrochemical response for F with anodic shifts,△Ep>214 mV. Addition of HSO4 induced dramatic cathodic peak current increase, which may be ascribed to consumption of the receptors in a reduction reaction, possibly hydrogenation at the iron centre. Hosts 8 displayed a "switched on" behavior in the fluorescent spectra on addition of F and AcO with fluorescence enhancement factors of 4 and 5 respectively, which allows the selectively sensing of them over other anions (Cl, Br, I-, HSO4-, H2PO4-). In addition, host 8 exhibited remarkable changes on addition of H2PO4 in the UV-vis spectra, a red shift of△λmax=8nm was observed.
In chapter three, we designed and synthesized three sensors 23,26,27 for "naked eye" detection of cyanide by utilizing azo dye or anthraquinone group as chromophores and a trifluoroacetyl group as an electrophile.1H NMR titration revealed that nucleophilic reaction of cyanide toward the electron-deficient carbonyl group was responsible for the color changes. In the case of compound 26, addition of cyanide has no obvious color changes even in a large excess, which can be ascribed to the strong intramolecular hydrogen bond between the NH and the anthraquinone oxygen, forming six-membered ring, hence the intermediate (cyanohydrin) can not be stabilized by the NH. Sensors 23,27 displayed great selectivity for the cyanide anion over other common inorganic anions in aqueous environment (H2O-CH3CN, 5:95) and can detect cyanide in water sample at micromolar concentrations. Our method is safe, fast, simple to use and inexpensive.
In the last part, a series of cyanine dyes were used to detect cyanide. The nucleophilic addition of cyanide to the iminium cation moiety achieved a specific sensing of this anion for the destruction of a largeπconjugation, leading to marked optical signal changes.28 and 29 can detect cyanide in common aprotic solvents or under CH2Cl2/H2O biphasic conditions with high selectivity and sensitivity. Unfortunately, poor cyanide sensing behavior was observed when water containing solvents was used. In contrast, hept-polymethine cyanine dye 30 can detect cyanide effectively in water containing solvents and Triton X-100 containing aqueous solution. The result that longer polymethine chain is favorable for the binding of cyanide is very important for the rational design of cyanine dye-based cyanide sensors.
The present sensing system has the following advantages:(1) our probes are commercially available; (2) the sensing of our probes are not affected by the common interferents such as F- and AcO-; (3) 29 and 30 are NIR sensors; (4) both the colorimetric and fluorescent detection limits of 29 and 30 are lower than Chinese government's guidelines of 1.9μM; In addition, both the colorimetric fluorescent detection limits of 30 for cyanide are less than 1.9μM via surfactant-assisted method.
引文
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